2-N-phenylbenzene-1,2-diamine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dissolving 4.4 g (24 mmol) of N-phenyl-1,2-phenylenediamine into 30 milliliter of N-methylpyrrolidone, 10 milliliter of 6-bromo picolinoyl chloride/N-methylpyrrolidone was dropped under cooling with ice. The resultant solution was further stirred at room temperature for 4 hours. After completion of the reaction, the reacted solution was poured into 400 milliliter of water and the resultant solution was further stirred. The resultant solids were separated by filtration, washed with water and methanol, dried under reduced pressure, thereby obtaining 4.5 g of 6-bromo-2′-(N-phenylamino)-picoline anilide (yield: 49%). was dropped under cooling with ice After completion of the reaction The resultant solids were separated by filtration washed with water and methanol dried under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Suspending 5.0 g (20 mmol) of 4-iodobenzoic acid into 50 milliliter of 1,2-dichloroethane, added 3 drops of N,N-dimethylformamide. Further adding 3.6 g (30 mmol) of thionyl chloride, the resultant suspension was refluxed with heating for 2 hours. Subsequently, removing the solvent by distillation, the residue was dissolved into 50 milliliter of N-methylpyrrolidone and then, further adding 3.7 g (20 mmol) of N-phenyl-1,2-phenylenediamine, the resultant solution was stirred at room temperature for 5 hours. After completion of the reaction, adding water and filtering the precipitated solid, washing with water and further with methanole, 8.0 g of crude 4-iodo-N-(2-phenylamino-phenyl)-benzamide was obtained. with heating for 2 hours Subsequently, removing the solvent by distillation the residue was dissolved into 50 milliliter of N-methylpyrrolidone After completion of the reaction filtering the precipitated solid washing with water and further with methanole

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Suspending 3.0 g (15 mmol) of 4-bromobenzoic acid into 30 milliliter of 1,2-dichloroethane, adding 2.7 g (23 mmol) of thionyl chloride and 3 drops of N,N-dimethylformamide, the resultant solution was stirred with heating at the temperature of about 50° C. for 1 hour and 30 minutes until benzoic acid as the material disappeared. After completion of the reaction, removing the solvent and excess thionyl chloride by distillation, dissolving the resultant acid chloride into 30 milliliter of N-methylpyrrolidone, adding 2.8 g (15 mmol) of N-phenyl-1,2-phenylenediamine, the resultant solution was stirred at room temperature for a night. After completion of the reaction, adding water and filtering the precipitated solid, further washing with water and by drying under reduced pressure, 5.2 g of 4-bromo-N-(2-phenylamino-phenyl)-benzamide was obtained. After completion of the reaction removing the solvent and excess thionyl chloride by distillation dissolving the resultant acid chloride into 30 milliliter of N-methylpyrrolidone After completion of the reaction filtering the precipitated solid further washing with water by drying under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 20 g (75.8 mmol) of 3,5-dibromobenzaldehyde and 16.8 g (90.9 mmol) of N-phenyl-o-phenylenediamine were dissolved in 150 mL of acetic acid. The solution was agitated at room temperature for 30 minutes. Next, 37 g (83.4 mmol) of lead (IV) acetate was added thereto. The resulting product was agitated at 50° C. for 1 hour. Then, water was poured into the acquired reactant. The resulting product was treated with ethyl acetate to perform extraction and the solvent was removed under reduced pressure. The extract was separated through a column and dried, gaining 9.5 g (Y=29%) of a yellow solid. The resulting product was agitated at 50° C. for 1 hour extraction the solvent was removed under reduced pressure The extract was separated through a column dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N1-phenylbenzene-1,2-diamine (4.15 g, 22 mmol) and benzaldehyde (2.1 g, 20 mmol) were mixed with methoxylethanol (60 ml) in a three-neck flask. The mixture was heated up to reflux for 48 hours. After cooled to room temperature, the solvent was evaporated. The residue was purified by column chromatography using dichloromethane to 5% of ethyl acetate in dichloromethane as eluent. 2 g of desired product was obtained. The mixture was heated up to reflux for 48 hours the solvent was evaporated The residue was purified by column chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of N-phenyl-o-phenylenediamine (1.84 g, 10 mmol) in diethyl ether (90 ml) was stirred at room temperature as 3,4,5-trimethoxybenzoyl chloride (2.31 g, 10 mmol) in diethyl ether (40 ml) was added dropwise. The reaction mixture was then stirred overnight at room temperature. The solvents were then removed in vacuo leaving N-[(3,4,5-trimethoxyphenyl)carbonyl]-N'-phenyl-phenylenediamine. was added dropwise The solvents were then removed in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of N-phenyl-o-phenylenediamine (10 mmol, 1.84 g) in 100 ml diethyl ether was stirred at room temperature as p-anisoyl chloride (1 mmol, 1.71 g) was added dropwise. The resulting mixture was stirred at room temperature for about 96 hours. A precipitate formed before half of the anisoyl chloride/diethyl ether was added. was added dropwise